tagTranssexuals & CrossdressersTrapped and Trained Ch. 03

Trapped and Trained Ch. 03


The next few days felt like a lifetime for me. I couldn't sleep at night - every time I closed my eyes, all I could see were replays of myself, dressed like a whore, being strapped to a padded sawhorse while it fucked me from both sides. Everything I ate and drank had a horrid aftertaste of that bastard's cum - it was as if that taste was permanently embedded in my ataste buds now. The back of my throat was sore so it hurt to speak and my pussy... no, my ass, as I had reverted back to calling it... was sore from the repeated violations it suffered.

I went through a list of possible ideas to stop this madness from progressing. Sadly, there was nothing I could do in terms of revenge. If I went to the police and they arrested him, then come 11 o'clock that night the scheduled email would be sent out to my entire contact list. He had sent me a copy of the email the night I returned home. He had made so many edits to it that it seemed like a well done porno production. He threw in some background music and even injected some sound effects that made it sound as if I were moaning at various times, begging for more cock in my holes and cum in my belly. To my horror, it was all extremely believable, especially since the second portion of the video was me seemingly voluntarily stuffing my holes with dildos and drinking glasses full of cum. Anyone who saw the video would view me as a willing participant to this twisted game he was playing.

Since I couldn't do anything that would leave him incapacitated or away from his home for an extended period of time, I was left with bargaining with him. I emptied out my bank account the day after my ordeal when I had made my decision., which wasn't as much as one would hope in this situation and only amounted to roughly over $4,000. Surely that would be enough to buy him off though, I convinced myself. I did not attempt to contact him, holding onto a foolish hope that he would possibly just forget about me. Three days passed when, finally, I received a message from him with a photo attachment that Saturday morning. The email read:


It has been a few days now, so I'm sure the reality of your situation has set in for you. By this time you should have accepted that you are now my property to do with as I please. I have given you these days to not only come to this realization, but also to recover from your first training session. I know it has been hard for you to go this long without the taste of cum or without a hard cock pumping in and out of that pussy of yours. You are such a slut, as evidenced in the attached photo.

But the time has come for your second training session, so your wait is finally over. You will be sure that your body is entirely smooth before coming to my house. You will step in the front door, strip, and then wait on all fours for your inspection. If you do not pass inspection, you will be locked out of the house fully nude and the email will be sent immediately to all of your contacts. You will have to find your own way home - and remember, the neighborhoods you'll have to navigate are not known for their hospitality.

You may want to shave twice, Candi. See you at 6pm, sharp.


Opening the picture attachment at the bottom of the note, my face burned in embarrassment as I saw the picture pop up on my screen. It was a closeup of my face after I had received my facial at the end of the training session involving the fucking machines. Cum was dripping down my face, my mascara was running and mixing in with it as it dripped down over my painted lips. I had to drive all the way home with that dried cum stuck to my face that night, and I spent easily over an hour in the shower once I returned home, using up all of my hot water in the process, but I didn't care. I just couldn't escape the feeling that I was missing a spot and would have a coworker notice it the next day at the office. I hated this man. I had to break free of his control. $4,000 had to be enough - what did he have to lose?

First I had to make sure I didn't get thrown out of his house before I even had the opportunity to negotiate with him. I went to the store and bought a women's razor, some body shaving cream and a women's scented lotion, my heart pounding as I checked out with the young and attractive cashier. I did as he said and shaved my entire body, twice. I then spread the lotion over my now smooth body, ending in the same soft and sensitive feeling that I remembered before. The only difference before was that I had no control over my body - this time I was the one doing everything to myself. How humiliating.

My heart was beating through my chest as I drove to the house where my nightmare previously took place. With $4,000 cash in my jeans pocket, I pulled in the driveway and walked to the front door. The door was unlocked, so I walked in and looked around. It was dark, but I noticed the familiar blinking red light of an activated video camera focused in on me. My body burned as I saw it, knowing that he was attempting to gain more control over me with more evidence. Part of me wanted to rip it off the wall, but I knew that was not an option under the circumstances. I slowly removed all of my clothes, leaving my jeans on top so I could easily get to my bargaining chip, then sunk to my hands and knees, waiting.

Almost immediately I heard the door to the basement open and the lights turned on. He walked over to me, but I kept my head down looking at the floor as I figured that's what I should do. He forcefully grabbed my hands and pulled them behind my back, clicking on some steel handcuffs tightly to my wrists. I figured this may be my last chance, so I started the negotiation process, or so I thought.

"Sir, may I please speak?" I timidly asked.

He ignored my request as he roughly felt around my body. Spreading my ass cheeks apart and fingering the outside of my hole, pulling on my cock and balls, pinching my nipples. He combed through my entire body without saying a word. Since he did not decline my request, I decided to take a chance.

"I would like to offer you a deal, Sir. In my jeans pocket, there is $4,000. It is yours. If you just allow me to watch you delete the videos and photos you have of me and let me go, then it is yours. It's all I have."

I heard a quiet chuckle come from the man's mouth.

"Oh Candi, you amuse me so. Don't you understand that you are worth so much more to me than a measly four grand? Hell, by the time I'm done with you, you'll be bringing twice that much a week when I rent that pussy of yours out to parties. No, you keep your money, slut. As I said before, I'm not interested in ruining you, just in using my property as I see fit."

I was speechless. I had spent the last few days convincing myself that he would take that deal. I spent the drive over here imagining him accepting, watching him delete all of his files, then sending me on my way, free from his control. Now he had declined, choosing instead to keep me as his property. I began to sob uncontrollably, which only seemed to anger him.

"Quit crying you little bitch, you should be glad I chose to keep you. I won't be keeping all of the money you earn, just my 90%. I believe I deserve that much since I'll be the one supplying your clothes and makeup, not to mention all the time and energy I'm giving to train you up to be the best cocksucking and fucking whore this town has ever seen. Now you get your shit together before I lose my temper and take it out on that ass of yours. You're lucky I haven't spanked you already for talking in that deep voice that has no place here. Now apologize to me for wasting my time and ask me to get on with your training, slut."

It took everything I had, but I pulled myself together. Mostly it was out of fear for not wanting one of his spankings, remembering how my entire ass felt like it had been held over a fire the last time I experienced one of those. Mustering up my best slutty voice like before, I asked...

"Sir, I am deeply sorry for wasting your valuable time and would love the opportunity to make things right. Please continue with my training as you had previously planned."

Suddenly he broke out into a smile, then quickly attached that familiar collar back on my neck with a leash leading off of it. Understanding that he now had complete control over me, he removed my handcuffs, apparently letting me know that I had passed his inspection. Next he pulled upward on the leash and gave the collar a short, sudden zap, signaling me to stand. I obliged, then followed him down the stairs to the basement/dungeon, trying to keep my mind from getting too far ahead of itself and not thinking about what was ahead of me tonight.

Once downstairs he led me to the center of the room. Looking up I could see shackles hanging from the ceiling, which he promptly placed my wrists in. My arms were still bent a bit, so he walked over to a crank and turned it a few times, pulling the chains tight and straightening out my arms. He came back over to me, wheeling a full length mirror in front of me and once again applied the tan colored paste to my genitals (after again going through the painful process of shoving my testicles up inside me) - when he was finished I again looked down to see what appeared at first glance to be a smoothly shaven, tanned pussy. He even cut a small slit down the middle to give the appearance of fat, swollen pussy lips. How thoughtful of him...

He then brought out a long blond wig that was split out into pigtails over to me. He placed it on my head and, after making his usual adjustments, secured it. After making me shake my head from side to side and then forward and backwards - "as if you were sucking a cock" - as he put it, he seemed satisfied and moved on to the next step in my transformation.

Next again was the makeup, which he expertly applied as previously done. A thick coat of foundation, some glittery pink eye shadow with thick mascara to again make my already long eyelashes stand out even more. Following that was some blush with more girly glitter mixed in with it. Next he applied what felt like three coats of lipstick followed by another two coats of lip gloss - again, with glitter mixed in. He stepped out of the way and I looked at my face. Whereas last time I was made to look like nothing but a whore that you would see on the side of the road, this time I was being made up to look younger. Still slutty, but almost like an 18 or 19 year old, immediately taking years off of my life with his handiwork. I finally understood why when he came back.

First, he again applied a heavy coat of the glue substance to my chest before sticking on the high C/low D implants to me. After holding them for a few minutes he let go and I felt the familiar weight sagging off of my chest. He then went to the box and started pulling out my outfit for the session. First was a white piece of material that was supposed to pass for a shirt, though it looked like little more than a bra that would tie in the middle. Next was an embarrassingly short plaid skirt with a black belt passing through it. When he held it up I could see that the belt buckle said "SLUT" in glittery silver letters as an extra touch. He then pulled out a black satin thong with white bows spread around the waistband, followed by a white garter belt with black bows and black ribboning down by the garter snaps. Next out of the box were some white stockings that had a black bow at the top, inside their frilly lace trim. Lastly were some white platform high heels. The spike seemed to be even higher on these and it looked as though I would almost have to stand on my tiptoes just to fit inside them. Where did he get all of this stuff, I wondered in my head.

Efficiently he placed the clothing on me. While putting on the thong I felt him grind his hard cock against my ass as he slid the string of the thong between my cheeks. He made me moan like a whore as he did it, reaching his hands around to feel my breasts. He finally stopped himself and went back to dressing me, finishing with the high heels that immediately made me feel like I had a cramp in my foot just by slipping them on. Walking would be difficult. He then snapped his fingers as if he had forgotten something and came back with a handful of small objects. Bending down, I again heard the familiar snaps of tiny padlocks being locked into place on my feet, again making my feet prisoners to these horrible contraptions.

My Master then released my arms from the shackles. It took a few minutes for the blood to rush back into my arms and hands, but he had no time to wait for that as he roughly pulled on the leash and sent some zaps through to my collar to spur me on. I fell a few times while learning to walk in these heels, but quickly learned that I needed to take smaller steps and walk in more of a straight line. Soon I was keeping pace with him just fine. As he walked me around the room, he made me talk in my slutty voice about how much of a whore I wanted to be, how I wanted nothing more than to have thick cocks shooting loads inside me, thanking him for this invaluable service he was giving me by training me. Inside I was screaming at him, cursing his very existance... but on the outside I had to keep up this persona of being some slutty school girl.

He would frequently stop and make me stand in awkward poses. Usually it involved me bending over and showing off my ass, obviously just more ammo that would be recorded by the multiple cameras in this room. Other times I would push my breasts together and pout my heavily painted lips, or lift up my skirt and make an O shape with my mouth, inviting cocks to penetrate it. Anything that came into his perverted mind, I would have to strike that pose, often times for minutes at a time while he walked circles around me, critiquing my form, adjusting my clothing or my hair or reapplying some of my makeup.

Finally he left me standing in the middle of the room as he went and retrieved a chair with a very high back that would easily go up past my head when seated. The chair had a hole in the bottom of it. He pulled down my thong to my knees, then made me sit down on the chair with my ass... pussy... centered directly over the hole. Once I was centered I watched as he methodically placed cuffs all over my body, securing me in place. My legs were fastened to the legs of the chair in four different locations, my arms cuffed behind me and fastened in place. Another two straps went over my lap, holding me down against the base of the chair snuggly. More straps held my chest against the back of the chair as one final strap went over my forehead and around the back, holding my head in place, unable to even move it side to side.

Into a closet my Master went, outside of my view. I heard something rolling towards me, but never actually saw it. It sounded like he was placing something underneath me. He frequently would poke a few fingers up through the hole and finger my pussy with a cold, greasy fluid - I assumed it was similar to before and he was lubing me up for the events to come. To my surprise I heard him walk away without anything penetrating my pussy, so I thought I was possibly mistaken as to what he had been doing. Back to the closet he went, this time coming back around with my worst nightmare.

Again, in front of me was the machine that abused my mouth the previous visit. Again I saw a full bag of the white sticky fluid attached to the dildo on the end of the machine through the tubing. He placed it in front of me, but in my mind I knew he had forgotten one thing. This time, I was not gagged with my mouth open. This time I would never open my mouth for that damned thing. I shut my mouth tightly. When my Master saw this, he gave that familiar chuckle as he lined up the dildo with my mouth and locked the machine in place on the ground. He pressed a few buttons and the dildo very slowly began to creep towards me, a tiny bit of precum starting to form at the tip.

"Same drill as before, Candi. Now open wide."

I did my best to shake my head and tell him no. The dildo was now inches from my face as I could smell the mixture of rubber and cum getting closer and closer. He came down next to my ear and whispered

"You can keep your mouth shut for a little while, but this machine will not stop pushing forward. Eventually the pain will either become too much or it will just knock your teeth out and make its way in that way. It's your decision, but I would suggest opening up and accepting it. Take the cock in your mouth, Candi, you know you want it."

I again tried to shake my head no, but it was no use, I was stuck. The dildo came in contact with my lips, gently at first, but slowly it started to increase the pressure. My lips were being smashed against my teeth now and the pain was unbearable. My mind wandered and I opened my mouth to scream, allowing the cock entry into my mouth. My lips came down around it as I moaned into it to express my pain. My Master just smiled with one of those "I told you so" smirks as he went back to the machine's panel and pressed more buttons, causing the dildo to now increase in pace. In and out it pumped, never going back far enough to leave my mouth and allow me to close it. I felt the impressions of the rubber veins sliding along my lips. Looking down at the black cock I could see hints of my pink lipstick and bits of glitter now showing while it slid in and out. The tip again began to hit the back of my throat, periodically triggering my gag reflex, but it never let up. Finally it went in to the hilt and gave that awful pause as I knew what was coming. I watched as the liquid flowed through the tubing and heard the machine whirl, then felt the stream of warm cum hit the back of my throat. It caused me to gag on the cock again but I could not move, so all I could do to stop the gagging was swallow the load that was now trapped in my mouth.

My Master came over to me and gave me an approving nod, then knelt beside me. Suddenly I heard a noise from underneath me and began to feel pressure against my pussy. Slowly but surely a cold metal object slid its way inside of me, then paused once fully impaled. To my shock and horror, the object began going through a wide range of activities over the next few minutes. First it would vibrate at such a rate that the entire chair was shaking. Next it felt like it would shift in temperature, from ice cold to red hot, making me squeal and try to squirm in the chair, doing anything to get the object out of me, but obviously to no use. Next it would start to move in small circles, brushing up and pushing out the edges of my pussy, obviously attempting to expand my hole. Finally it would pump in and out of my ass at a rapid pace until it extracted itself altogether. At random increments it would start again, never with the same pattern of activities.

My Master again appeared at my side and whispered words that will haunt me late at night for sure...

"You see Candi, you need to get used to performing these whore acts in different positions. You won't always be laying doggy style for your future clients - sometimes you will be bouncing your pussy up and down on a cock while taking another in your mouth, understand? It's all a part of your training. Now, this bag is a bit larger than the one from last time, so I think you should be all set down here for at least two hours. That machine training your pussy is one of my favorites - it took me a long time to get it just right, but it should do wonders for training your pussy efficiently. By the time it's finished you'll be well on your way to being an expert at having a cock in your ass and all the different experiences you can feel while one is inside of you. And we can't forget to let you enjoy the show."

With all that said and still echoing in my mind, he clicked a button on a remote and again I saw the television display of my misery. There was again a close up shot of the dildo assaulting my mouth, only this time it looked more voluntary as there was no longer a gag forcing my mouth open. It looked as though I opened my mouth and took the cock in on my own. There was a close up shot showing the hole leading to my pussy with a light shining on the hole in the chair to better see the metal dildo hooked into the machine gaining access and exiting my pussy as you watched the rod spin and rotate while I was impaled on the dildo at the end. Then there were multiple shots of the entire scene so you could see me dressed in my full outfit, from my glittery makeup and pigtails, to the white shirt straining against the knot to hold in my breasts, to the glittery "SLUT" belt buckle holding up my tiny plaid skirt. Periodically the camera would zoom in on my crotch, allowing you to see the slit in my pussy. It would then pan back out and you would see my black thong pulled halfway down my legs, over my white stockings and then leading down to my feet uncomfortably resting on the ground inside the padlocked heels.

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bySissyIndy© 11 comments/ 235353 views/ 60 favorites

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